Recently Sold Osprey, FL Homes

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  $950,000 Sold Apr 29, 2025

  32 Bayhead Ln, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 2,570 Sq Ft
  • Built 1993

  Last Sold Summary

  • 21% Below List Price
  • $370/SF
  • 82 Days On Market

  Current Estimated Value $902,491

  Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  32 Bayhead Ln, Osprey, FL 34229
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  $5,350,000 Sold Dec 08, 2025

  622 Bayshore Dr, Osprey, FL 34229

  • 6 Beds
  • 5 Baths
  • 4,893 Sq Ft
  • Built 2022

  Last Sold Summary

  • 21% Below List Price
  • $1,093/SF
  • 126 Days On Market

  Current Estimated Value $5,283,398

  Last Listing Agent Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY

  622 Bayshore Dr, Osprey, FL 34229
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  $160,000 Sold Dec 22, 2025

  191 Palm Air Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,376 Sq Ft
  • Built 1978

  Last Sold Summary

  • 29% Below List Price
  • $116/SF
  • 518 Days On Market

  Last Listing Agent John Alexander FINE PROPERTIES

  191 Palm Air Dr, Osprey, FL 34229
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  $435,000 Sold Feb 20, 2026

  1102 Jessie Harbor Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,425 Sq Ft
  • Built 2004

  Last Sold Summary

  • 8% Below List Price
  • $305/SF
  • 9 Days On Market

  Current Estimated Value $444,124

  Last Listing Agent Mackenzie Davis-Mahan DOWNING FRYE REALTY, INC.

  1102 Jessie Harbor Dr, Osprey, FL 34229
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  $295,000 Sold Nov 14, 2025

  4267 Expedition Way, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft
  • Built 2017

  Last Sold Summary

  • 5% Below List Price
  • $260/SF
  • 87 Days On Market

  Current Estimated Value $281,389

  Last Listing Agent Judi Cipollina COLDWELL BANKER REALTY

  4267 Expedition Way, Osprey, FL 34229
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  $807,000 Sold Apr 22, 2025

  124 Tina Island Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,112 Sq Ft
  • Built 1975

  Last Sold Summary

  • 31% Below List Price
  • $382/SF
  • 244 Days On Market

  Current Estimated Value $811,429

  Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

  124 Tina Island Dr, Osprey, FL 34229
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  $275,000 Sold Apr 11, 2025

  208 Pennsylvania Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 900 Sq Ft
  • Built 1963

  Last Sold Summary

  • 8% Below List Price
  • $306/SF
  • 33 Days On Market

  Current Estimated Value $281,837

  Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

  208 Pennsylvania Ave, Osprey, FL 34229
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  $560,000 Sold Mar 31, 2026

  409 N Point Rd Unit 603, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,203 Sq Ft
  • Built 2004

  Last Sold Summary

  • 29% Below List Price
  • $254/SF
  • 727 Days On Market

  Current Estimated Value $664,712

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 603, Osprey, FL 34229
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  $140,000 Sold Dec 12, 2025

  570 Blackburn Point Rd Unit 19, Osprey, FL 34229

  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • 59 Days On Market

  Current Estimated Value $140,434

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 19, Osprey, FL 34229
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  $875,000 Sold May 01, 2025

  851 E Bay St, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,329 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $376/SF
  • 8 Days On Market

  Current Estimated Value $863,715

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  851 E Bay St, Osprey, FL 34229
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  $395,000 Sold Jun 16, 2025

  109 Burney Rd, Osprey, FL 34229

  • Land
  • 0.52 Acre
  • $759,615 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 30 Days On Market

  Current Estimated Value $385,951

  Last Listing Agent Lori Madden MANGROVE REALTY ASSOCIATES

  109 Burney Rd, Osprey, FL 34229
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  $527,500 Sold Sep 11, 2025

  1164 Beachcomber Ct Unit 19, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 1,952 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $270/SF
  • 60 Days On Market

  Current Estimated Value $501,511

  Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

  1164 Beachcomber Ct Unit 19, Osprey, FL 34229
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  $850,000 Sold Dec 17, 2025

  678 Crane Prairie Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,483 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $342/SF
  • 4 Days On Market

  Current Estimated Value $842,202

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  678 Crane Prairie Way, Osprey, FL 34229
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  $2,189,000 Sold Feb 09, 2026

  370 Sugar Mill Dr, Osprey, FL 34229

  • 5 Beds
  • 5.5 Baths
  • 4,783 Sq Ft
  • Built 1996

  Last Sold Summary

  • 11% Below List Price
  • $458/SF
  • 0 Days On Market

  Current Estimated Value $2,211,758

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  370 Sugar Mill Dr, Osprey, FL 34229
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  $645,000 Sold Aug 25, 2025

  1212 Windward Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,994 Sq Ft
  • Built 1982

  Last Sold Summary

  • 17% Below List Price
  • $323/SF
  • 174 Days On Market

  Current Estimated Value $661,457

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  1212 Windward Dr, Osprey, FL 34229
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  $150,000 Sold Jul 25, 2025

  107 Woodland Place Unit 107, Osprey, FL 34229

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft
  • Built 1979

  Last Sold Summary

  • 11% Below List Price
  • $173/SF
  • 49 Days On Market

  Current Estimated Value $145,931

  Last Listing Agent Carla Rayman Kidd COLDWELL BANKER REALTY

  107 Woodland Place Unit 107, Osprey, FL 34229
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  $200,000 Sold Dec 09, 2025

  201 Woodland Dr Unit 201, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1980

  Last Sold Summary

  • 33% Below List Price
  • $152/SF
  • 346 Days On Market

  Current Estimated Value $200,710

  Last Listing Agent Lauren Meadows PREFERRED PROPERTIES OF VENICE INC

  201 Woodland Dr Unit 201, Osprey, FL 34229
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  $1,014,000 Sold Nov 12, 2025

  201 Eaglenook Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,379 Sq Ft
  • Built 1992

  Last Sold Summary

  • 16% Below List Price
  • $300/SF
  • 211 Days On Market

  Current Estimated Value $1,045,713

  Last Listing Agent Dawn Bear WILLIAM RAVEIS REAL ESTATE

  201 Eaglenook Way, Osprey, FL 34229
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  $200,000 Sold Oct 06, 2025

  444 Washington Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 1953

  Last Sold Summary

  • 20% Below List Price
  • $156/SF
  • 9 Days On Market

  Current Estimated Value $218,887

  Last Listing Agent Hansel Pitts COLDWELL BANKER SARASOTA CENT.

  444 Washington Ave, Osprey, FL 34229
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  $855,000 Sold May 30, 2025

  14021 Bellagio Way Unit 311, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 2,235 Sq Ft
  • Built 2006

  Last Sold Summary

  • 14% Below List Price
  • $383/SF
  • 211 Days On Market

  Current Estimated Value $790,037

  Last Listing Agent Kristin O'Connor GULF TO BAY SOTHEBY'S INTERNAT

  14021 Bellagio Way Unit 311, Osprey, FL 34229
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  $525,000 Sold Sep 30, 2025

  116 Villa Dr Unit 116, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,221 Sq Ft
  • Built 1968

  Last Sold Summary

  • $430/SF
  • 2 Days On Market

  Current Estimated Value $485,058

  Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

  116 Villa Dr Unit 116, Osprey, FL 34229
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  $440,000 Sold Sep 22, 2025

  9528 Knightsbridge Cir, Sarasota, FL 34238

  • 4 Beds
  • 2.5 Baths
  • 3,008 Sq Ft
  • Built 1992

  Last Sold Summary

  • 27% Below List Price
  • $146/SF
  • 59 Days On Market

  Current Estimated Value $466,044

  Last Listing Agent Michelle Hupp KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  9528 Knightsbridge Cir, Sarasota, FL 34238
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  $255,000 Sold Jan 12, 2026

  106 Raphael Place, Nokomis, FL 34275

  • 3 Beds
  • 2 Baths
  • 1,839 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Above List Price
  • $139/SF
  • 12 Days On Market

  Current Estimated Value $265,377

  Last Listing Agent Tracey Punzone UKEEPCOMMISSION REAL ESTATE

  106 Raphael Place, Nokomis, FL 34275
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  $1,210,000 Sold Jan 27, 2026

  8974 Wildlife Loop, Sarasota, FL 34238

  • 4 Beds
  • 3.5 Baths
  • 3,979 Sq Ft
  • Built 2004

  Last Sold Summary

  • 7% Below List Price
  • $304/SF
  • 15 Days On Market

  Current Estimated Value $1,222,813

  Last Listing Agent Cynthia Bowers COLDWELL BANKER SARASOTA CENT.

  8974 Wildlife Loop, Sarasota, FL 34238
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  $680,000 Sold Apr 01, 2026

  5400 Lampiasi St, Sarasota, FL 34238

  • 2 Beds
  • 2 Baths
  • 1,682 Sq Ft
  • Built 2020

  Last Sold Summary

  • 9% Below List Price
  • $404/SF
  • 58 Days On Market

  Current Estimated Value $732,887

  Last Listing Agent Mark Quire KELLER WILLIAMS ON THE WATER S

  5400 Lampiasi St, Sarasota, FL 34238
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  $2,555,000 Sold Apr 21, 2025

  12000 Trails Reserve Ct, Sarasota, FL 34238

  • 4 Beds
  • 6 Baths
  • 4,493 Sq Ft
  • Built 2019

  Last Sold Summary

  • $569/SF

  Current Estimated Value $2,379,884

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  12000 Trails Reserve Ct, Sarasota, FL 34238
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  $621,000 Sold Sep 15, 2025

  9492 Forest Hills Cir, Sarasota, FL 34238

  • 2 Beds
  • 2 Baths
  • 1,766 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Below List Price
  • $352/SF
  • 25 Days On Market

  Current Estimated Value $602,101

  Last Listing Agent Mimi Kruk MICHAEL SAUNDERS & COMPANY

  9492 Forest Hills Cir, Sarasota, FL 34238
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  $2,535,000 Sold Feb 27, 2026

  5305 Brookgrove Dr, Sarasota, FL 34238

  • 4 Beds
  • 6 Baths
  • 4,938 Sq Ft
  • Built 2021

  Last Sold Summary

  • 1% Below List Price
  • $513/SF
  • 2 Days On Market

  Current Estimated Value $2,496,855

  Last Listing Agent Ross Fishman FISHMAN GROUP REALTY LLC

  5305 Brookgrove Dr, Sarasota, FL 34238
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  $1,000,000 Sold Jul 11, 2025

  5255 Cicerone St, Sarasota, FL 34238

  • 3 Beds
  • 3.5 Baths
  • 2,103 Sq Ft
  • Built 2021

  Last Sold Summary

  • 5% Below List Price
  • $476/SF
  • 98 Days On Market

  Current Estimated Value $982,379

  Last Listing Agent Bill McCue BRIGHT REALTY

  5255 Cicerone St, Sarasota, FL 34238
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  $450,000 Sold Apr 18, 2025

  103 Raphael Place, Nokomis, FL 34275

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft
  • Built 1984

  Last Sold Summary

  • 14% Below List Price
  • $238/SF
  • 79 Days On Market

  Current Estimated Value $447,999

  Last Listing Agent Kelly Gitt KELLER WILLIAMS ON THE WATER

  103 Raphael Place, Nokomis, FL 34275
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  $700,000 Sold Sep 05, 2025

  5324 Popoli Way, Sarasota, FL 34238

  • 3 Beds
  • 2 Baths
  • 1,918 Sq Ft
  • Built 2020

  Last Sold Summary

  • 3% Below List Price
  • $365/SF
  • 3 Days On Market

  Current Estimated Value $689,751

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  5324 Popoli Way, Sarasota, FL 34238
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  $665,000 Sold Jan 26, 2026

  5301 Bartolomeo St, Sarasota, FL 34238

  • 3 Beds
  • 2 Baths
  • 1,918 Sq Ft
  • Built 2020

  Last Sold Summary

  • 10% Below List Price
  • $347/SF
  • 216 Days On Market

  Current Estimated Value $665,381

  Last Listing Agent Anne Friedland BLUESRQ REAL ESTATE INC

  5301 Bartolomeo St, Sarasota, FL 34238

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